Lipase-catalyzed polycondensation of dicarboxylic acid-divinyl esters and glycols to aliphatic polyesters

Uyama, Hiroshi; Yaguchi, Shigeru; Kobayashi, Shiro

doi:10.1002/(sici)1099-0518(19990801)37:15<2737::aid-pola7>3.0.co;2-m

Cited by 59 publications

(59 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…PBS, POA, and POS were synthesized by the lipase-catalyzed polycondensation of the corresponding divinyl esters and glycols according to the literature. [35] Lipases CA and MM were kindly donated by Novozymes Japan Ltd. Lipase PC was a gift from used as received. Lipases were used without further purification.…”

Section: Experimental Partmentioning

confidence: 99%

Lipase-Catalyzed Transesterification of Polyesters to Ester Copolymers

et al. 2001

Self Cite

View full text Add to dashboard Cite

Section: Experimental Partmentioning

confidence: 99%

Lipase-Catalyzed Transesterification of Polyesters to Ester Copolymers

et al. 2001

Self Cite

View full text Add to dashboard Cite

“…Similar results were obtained in the enzymatic synthesis of aliphatic polyesters from divinyl esters. 30 The polymerization in toluene afforded the polymer in a moderate yield, however, the molecular weight of the resulting polymer was relatively low (entry 10). It is to be noted that toluene afforded no polymeric materials from a combination of ld and 2c.…”

Section: Enzymatic Polymerization Of Divinyl Isophthalate and Rtw-mentioning

confidence: 99%

“…It is to be noted that toluene afforded no polymeric materials from a combination of ld and 2c. 30 No polymers were obtained in acetonitrile and THF (entries 3 and 9). This may be due to the inactivation of the enzyme in polar organic solvents.…”

Section: Enzymatic Polymerization Of Divinyl Isophthalate and Rtw-mentioning

confidence: 99%

“…2 7 -29 We have performed the systematic investigation on the effects of the reaction parameters in the lipase-catalyzed polymerization of dicarboxylic acid divinyl esters and cx,w-glycols, yielding aliphatic polyesters with different methylene chain length. 30 This study deals with enzymatic synthesis of polyesters having an aromatic moiety in the main chain from divinyl esters and glycols (Scheme 1). Relevant to this study, there are two reports available on the enzymatic synthesis of aromatic polyesters.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Enzymatic Synthesis of Aromatic Polyesters by Lipase-Catalyzed Polymerization of Dicarboxylic Acid Divinyl Esters and Glycols

Uyama

Yaguchi

Kobayashi

1999

Polym J

Self Cite

View full text Add to dashboard Cite

ABSTRACT:Polyesters containing aromatic moiety in the main chain have been synthesized by enzymatic polymerization of dicarboxylic acid divinyl esters and glycols under mild reaction conditions. Divinyl esters of isophthalic acid, terephthalic acid, and p-phenylene diacetic acid, were used as new monomer for the enzymatic polymerization. Effects of the polymerization conditions were systematically investigated in the polymerization of divinyl isophthalatc and 1,6-hcxancdiol. Candida antarctica lipase afforded the polymer of the highest molecular weight. Methylene chain length of the glycol affected the polymer yield and molecular weight. Divinyl terephthalate was enzymatically polymerized under the similar reaction conditions, yielding the polymer of lower molecular weight. Enzymatic polymerization of divinyl sebacate and p-xylylene glycol also afforded the aromatic polyester.KEY WORDS Enzymatic Polymerization I Lipase I Aromatic Polyester I Divinyl Ester I Polycondensation I Aromatic polyesters, typically poly(ethylene terephthalate) (PET) and poly(butylene terephthalate) (PBT), are widely used in various fields since they have excellent properties, e.g., high thermal and chemical stabilities.1.2 These polymers are industrially produced at high temperature under reduced pressure. Since PET and PBT are not environmentally benign due to their low biodegradability, aliphatic and aromatic ester copolymers have been developed as new biodegradable engineering plastics. However, their synthesis also involved severe reaction conditions (high temperature and/or reduced pressure).Recently, hydrolase-catalyzed polymerizations have received much attention as environmentally friendly methodology of polyester syntheses owing to non-toxic enzyme catalyst and mild reaction conditions. 3 -7 In some cases, lipase showed unique catalytic behaviors for the polyester syntheses in comparison with those of conventional chemical catalysts. Lipase induced the ring-opening polymerization of small-and medium-size lactones as well as macrolides (12-, 13-, 16-, and 17-membered lactones). 8 -17 Using traditional chemical catalysts, the macrolides showed much lower reactivity and polymerizability than e-caprolactone (7-membered lactone, e-CL) due to their lower ring strain. 18 • 19 However, they were enzymatically polymerized much faster than e-CL, probably due to the stronger recognition of the macrolide by lipase. 13 -17 In lipase-catalyzed acylation for synthesis of functional organic products, vinyl esters have been often used as acylating agents because the irreversible tautomerization of the leaving vinyl alcohol group to acetaldehyde afforded the desired product in high yields. 20 • 21 We reported that divinyl adipate was superior to the corresponding diacid or dialkyl ester for the enzymatic synthesis of polyester. 22 Afterwards, several examples of the enzymatic polymerizations using divinyl esters were t To whom correspondence should be addressed. 380reported. 23 -25 Very recently, we have found that the lipase-catalyzed pol...

show abstract

“…[23,29,36] Poly(l-lactide) was prepared by ring-opening polymerization of l-lactide using tin(II) 2-ethylhexanoate. [37] Poly(1,2-propylene carbonate) was purchased from Aldrich Chemical Co. Lipase PF was kindly donated by Amano Pharmaceutical Co. and used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Lipase-Catalyzed Ring-Opening Polymerization of Lactones in the Presence of Aliphatic Polyesters to Ester Copolymers

Namekawa

Uyama

Kobayashi³

2001

Macromol. Chem. Phys.

Self Cite

View full text Add to dashboard Cite

Ring‐opening polymerization of macrolides in the presence of aliphatic polyesters has been performed using Pseudomonas lipase as catalyst to produce ester copolymers with molecular weights of several thousands. The polymerization behavior was monitored by SEC and NMR. 13C NMR analysis showed that the resulting polymer was not a mixture of the starting polyester and the polymer from the macrolide, but a random copolymer consisting of both units. These data indicate that the lipase catalyzed the polymerization of the macrolide as well as the intermolecular transesterification of the starting and resulting polymers. The random copolymer was found to be highly crystalline by DSC and WAXD measurement. The present specific catalysis of the lipase was applied to the synthesis of ester copolymers by transesterification between two different polyesters.

show abstract

Lipase-catalyzed polycondensation of dicarboxylic acid-divinyl esters and glycols to aliphatic polyesters

Cited by 59 publications

References 26 publications

Lipase-Catalyzed Transesterification of Polyesters to Ester Copolymers

Lipase-Catalyzed Transesterification of Polyesters to Ester Copolymers

Enzymatic Synthesis of Aromatic Polyesters by Lipase-Catalyzed Polymerization of Dicarboxylic Acid Divinyl Esters and Glycols

Lipase-Catalyzed Ring-Opening Polymerization of Lactones in the Presence of Aliphatic Polyesters to Ester Copolymers

Contact Info

Product

Resources

About